0000000001299849

AUTHOR

Stefan Kubik

showing 14 related works from this author

Synthesis and Structural Characterization of a Cyclen-Derived Molecular Cage

2015

Reaction of a tetrafunctionalized cyclen derivative containing four aldehyde groups with an appropriate diamine followed by reduction and demetalation highly efficiently affords a bis(cyclen)-derived molecular cage. Potentiometric investigations show that this compound forms dimetallic complexes with copper(II), with the two metal ions selectively coordinated to the cyclen units. X-ray crystallography indicates that these complexes could give rise to new cascade complexes after incorporation of anions between the metal centers.

chemistry.chemical_classificationStereochemistryChemistryMetal ions in aqueous solutionOrganic ChemistryPotentiometric titrationchemistry.chemical_elementBiochemistryCopperAldehydeMetalchemistry.chemical_compoundCyclenvisual_artDiaminePolymer chemistryvisual_art.visual_art_mediumPhysical and Theoretical ChemistryDerivative (chemistry)Organic Letters
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Efficient stabilisation of a dihydrogenphosphate tetramer and a dihydrogenpyrophosphate dimer by a cyclic pseudopeptide containing 1,4-disubstituted …

2017

A cyclic pseudooctapeptide 2 is described containing 1,4-disubstituted 1,2,3-triazole moieties. This compound features eight converging hydrogen bond donors along the ring, namely four amide NH and four triazole CH groups, which enable 2 to engage in interactions with anions. While fully deprotonated sulfate anions exhibit only moderate affinity for 2, protonated anions such as dihydrogenpyrophosphate and dihydrogenphosphate anions are strongly bound. Complexation of the phosphate-derived anions involves sandwiching of a dihydrogenpyrophosphate dimer or a dihydrogenphosphate tetramer between two pseudopeptide rings. X-ray crystallography provided structural information, while 1H NMR spectro…

fosfaatit010405 organic chemistryStereochemistryChemistryHydrogen bondDimerTriazoleIsothermal titration calorimetryProtonationGeneral Chemistry010402 general chemistry01 natural sciencesphosphate oligomers0104 chemical sciencesoligomeeriCrystallographychemistry.chemical_compoundDeprotonationpseudopeptidesTetramerAmidestabilisationta116orgaaniset yhdisteetChemical Science
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Oxoanion binding to a cyclic pseudopeptide containing 1,4-disubstituted 1,2,3-triazole moieties

2016

A macrocyclic pseudopeptide 3 is described featuring three amide groups and three 1,4-disubstituted 1,2,3-triazole units along the ring. This pseudopeptide was designed such that the amide NH groups and the triazole CH groups converge toward the cavity, thus creating an environment well suited for anion recognition. Conformational studies in solution combined with X-ray crystallography confirmed this preorganisation. Solubility of 3 restricted binding studies to organic media such as 5 vol% DMSO/acetone or DMSO/water mixtures with a water content up to 5 vol%. These binding studies demonstrated that 3 binds to a variety of inorganic anions in DMSO/acetone including chloride, nitrate, sulfat…

010405 organic chemistryChemistryStereochemistryDimerOrganic ChemistryTriazoleoxoanion bindings010402 general chemistry01 natural sciencesBiochemistryChlorideMedicinal chemistry0104 chemical scienceschemistry.chemical_compoundpseudopeptidesStability constants of complexesAmidemedicineMoleculePhysical and Theoretical ChemistrySulfateSolubilityta116medicine.drugOrganic & Biomolecular Chemistry
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Efficient stabilisation of a dihydrogenphosphate tetramer and a dihydrogenpyrophosphate dimer by a cyclic pseudopeptide containing 1,4-disubstituted …

2017

A cyclic pseudooctapeptide binds a dihydrogenpyrophosphate dimer or a cyclic dihydrogenphosphate tetramer by sandwiching these anionic aggregates between two pseudopeptide rings.

ChemistryChemical Science
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Efficient stabilisation of a dihydrogenphosphate tetramer and a dihydrogenpyrophosphate dimer by a cyclic pseudopeptide containing 1,4-disubstituted …

2017

A cyclic pseudooctapeptide 2 is described containing 1,4-disubstituted 1,2,3-triazole moieties. This compound features eight converging hydrogen bond donors along the ring, namely four amide NH and four triazole CH groups, which enable 2 to engage in interactions with anions. While fully deprotonated sulfate anions exhibit only moderate affinity for 2, protonated anions such as dihydrogenpyrophosphate and dihydrogenphosphate anions are strongly bound. Complexation of the phosphate-derived anions involves sandwiching of a dihydrogenpyrophosphate dimer or a dihydrogenphosphate tetramer between two pseudopeptide rings. X-ray crystallography provided structural information, while 1 H NMR spectr…

oligomeeripseudopeptidesfosfaatitstabilisationorgaaniset yhdisteetphosphate oligomers
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CCDC 1431346: Experimental Crystal Structure Determination

2015

Related Article: Alexander Ganß, Raquel Belda, Javier Pitarch, Richard Goddard, Enrique García-España, and Stefan Kubik|2015|Org.Lett.|17|5850|doi:10.1021/acs.orglett.5b03027

14174043-Tetraoxa-14112027303746-octaazaheptacyclo[28.22.2.2427.269.22225.23235.24851]tetrahexaconta-6822243234485055576163-dodecaeneSpace GroupCrystallographyCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 1555956: Experimental Crystal Structure Determination

2017

Related Article: Disha Mungalpara, Arto Valkonen, Kari Rissanen, Stefan Kubik|2017|Chemical Science|8|6005|doi:10.1039/C7SC02700A

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parametersbis(tetra-n-butylammonium) dihydrogen diphosphate 6183042-tetramethyl-345815161720272829323940414449515355-icosa-azanonacyclo[43.3.1.125.1913.11417.12125.12629.13337.13841]hexapentaconta-1(49)2(56)39(55)101214(54)1521(53)222426(52)2733(51)343638(50)394547-icosaene-7193143-tetrone 4-hydroxy-4-methylpentan-2-one acetone unknown solvate hydrateExperimental 3D Coordinates
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CCDC 1505706: Experimental Crystal Structure Determination

2016

Related Article: Disha Mungalpara, Harald Kelm, Arto Valkonen, Kari Rissanen, Sandro Keller, Stefan Kubik|2017|Org.Biomol.Chem.|15|102|doi:10.1039/C6OB02172G

Space GroupCrystallography(RRR)-61830-trimethyl-34581516172027282932373941-pentadeca-azaheptacyclo[31.3.1.125.1913.11417.12125.12629]dotetraconta-1(37)2(42)39(41)101214(40)1521(39)222426(38)273335-pentadecaene-71931-trione dimethyl sulfoxide solvate hydrateCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 1429442: Experimental Crystal Structure Determination

2015

Related Article: Alexander Ganß, Raquel Belda, Javier Pitarch, Richard Goddard, Enrique García-España, and Stefan Kubik|2015|Org.Lett.|17|5850|doi:10.1021/acs.orglett.5b03027

Space GroupCrystallography(mu-1417404366699295-octaoxa-1420273037535672798289-dodecaaza-11466398-tetraazoniatridecacyclo[54.48.2.2453.269.22225.22782.23079.23235.24851.25861.27477.28487.2100103]octacosahecta-68222432344850586074768486100102107109115117121123125127-tetracosaene)-dichloro-di-copper(ii) hexachloride nonahydrateCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 1555958: Experimental Crystal Structure Determination

2017

Related Article: Disha Mungalpara, Arto Valkonen, Kari Rissanen, Stefan Kubik|2017|Chemical Science|8|6005|doi:10.1039/C7SC02700A

Space GroupCrystallographyCrystal Systembis(tetra-n-butylammonium) 6183042-tetramethyl-345815161720272829323940414449515355-icosaazanonacyclo[43.3.1.125.1913.11417.12125.12629.13337.13841]hexapentaconta-1(49)2(56)39(55)101214(54)1521(53)222426(52)2733(51)343638(50)394547-icosaene-7193143-tetrone bis(dihydrogen phosphate) dimethyl sulfoxide unknown solvateCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 1504361: Experimental Crystal Structure Determination

2016

Related Article: Disha Mungalpara, Harald Kelm, Arto Valkonen, Kari Rissanen, Sandro Keller, Stefan Kubik|2017|Org.Biomol.Chem.|15|102|doi:10.1039/C6OB02172G

Space GroupCrystallographyCrystal Systemtris(tetra-n-butylammonium) bis(61830-trimethyl-34581516172027282932373941-pentadecaazaheptacyclo[31.3.1.125.1913.11417.12125.12629]dotetraconta-1(37)2(42)39(41)101214(40)1521(39)222426(38)273335-pentadecaene-71931-trione) tris(dihydrogen phosphate) dimethyl sulfoxide solvate hydrateCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 1431345: Experimental Crystal Structure Determination

2015

Related Article: Alexander Ganß, Raquel Belda, Javier Pitarch, Richard Goddard, Enrique García-España, and Stefan Kubik|2015|Org.Lett.|17|5850|doi:10.1021/acs.orglett.5b03027

Space GroupCrystallography44'4''4'''-(14710-tetraazacyclododecane-14710-tetrayltetrakis(methylene))tetrabenzaldehydeCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 1555957: Experimental Crystal Structure Determination

2017

Related Article: Disha Mungalpara, Arto Valkonen, Kari Rissanen, Stefan Kubik|2017|Chemical Science|8|6005|doi:10.1039/C7SC02700A

Space GroupCrystallographybis(tetra-n-butylammonium) dihydrogen diphosphate 6183042-tetramethyl-345815161720272829323940414449515355-icosa-azanonacyclo[43.3.1.125.1913.11417.12125.12629.13337.13841]hexapentaconta-1(49)2(56)39(55)101214(54)1521(53)222426(52)2733(51)343638(50)394547-icosaene-7193143-tetrone dimethyl sulfoxide unknown solvate hydrateCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 1555955: Experimental Crystal Structure Determination

2017

Related Article: Disha Mungalpara, Arto Valkonen, Kari Rissanen, Stefan Kubik|2017|Chemical Science|8|6005|doi:10.1039/C7SC02700A

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parametersbis(tetra-n-butylammonium) dihydrogen diphosphate 6183042-tetramethyl-345815161720272829323940414449515355-icosa-azanonacyclo[43.3.1.125.1913.11417.12125.12629.13337.13841]hexapentaconta-1(49)2(56)39(55)101214(54)1521(53)222426(52)2733(51)343638(50)394547-icosaene-7193143-tetrone unknown solvateExperimental 3D Coordinates
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